How to Money – Friday Flight: Forgotten 401k, Peaking Pessimism, & Loyalty is for Losers (#1032)

Hosts: Joel and Matt
Podcast: How to Money (iHeartPodcasts)
Date: September 5, 2025

Overview

In this "Friday Flight" episode, Joel and Matt tackle timely personal finance headlines and trends, mixing practical advice with their trademark banter and optimism. The main themes are: the challenge of forgotten 401(k)s, why investing feels uneasy even as markets hit highs, growing skepticism around the American dream and hard work, and why loyalty to consumer brands and banks often works against you. The hosts sprinkle in stories about backpacking, investing psychology, Gen Z entrepreneurship, and clever travel booking, always pushing listeners to think intentionally about their financial choices.

Key Topics & Insights

1. Simplicity, Minimalism, and Finding Happiness

(03:06–08:21)

• Joel’s backpacking trip in California prompts a reflection on how less is often more—stripping life to basics led to greater appreciation for community and amenities like “indoor plumbing.”
• Minimalism as a happiness hack: It’s not about fewer possessions for the sake of trend, but “how you spend your time and who you spend it with” (05:21–06:17).
• Personal Finance Takeaway: Cutting unnecessary expenses and seeking deeper meaning in how we use money is as important as what we buy.

Notable quote:

“Connection matters more than stuff.” — Joel (06:17)

2. Market Highs, Investing Anxiety, and the Explosion of ETFs

(08:21–14:59)

• Stock market at record highs – The S&P 500 is “kind of frothy,” and even seasoned investors are slightly shifting allocations—but not panicking or abandoning stocks.
• Nick Magiulli (friend of the show): Even experts are making only “slight changes” to allocations because of life changes (buying a home), not just market timing.
  (09:36: “He’s only making a slight change... it’s because of his own goals are changing”)
• The illusion of choice: There are now “more ETFs than individual stocks,” causing analysis paralysis—Joel wishes investing “looked more like Aldi” with fewer choices.
  (13:39-14:21)
• Actionable Summary: Stick with low-cost, diversified index funds (VOO, FZROX), don’t stress over industry-specific ETFs.

Notable quotes:

“Stay the course, man.” — Matt (10:21)
“I wish that for individual investors it looked more like Aldi where you walk in and there’s just fewer choices.” — Joel (14:21)

3. The Problem of Forgotten 401(k)s

(14:59–16:48)

• $1.7 trillion in “lost” 401(k) accounts — often forgotten at previous employers.
• Action Steps:
  • Check unclaimedretirementbenefits.com.
  • Companies like Capitalize can help you find and roll over old accounts.
• Key Point: Compounding works even when you’re not looking, but don’t forget to reclaim or consolidate your money!

4. Peaking Pessimism: Has the American Dream Disappeared?

(17:16–23:48)

• Wall Street Journal survey: 70% of Americans now doubt hard work alone achieves the American dream—down from 75% believing the opposite in 2000.
• Reasons cited:
  • Inflation and stagnant wages
  • Housing market barriers
  • Social comparison fueled by social media
  • Generational shifts in aspiration (Gen Z “zigs while others zag”)
• Hosts’ Response: There are significant obstacles, but “pessimism can be this self-fulfilling prophecy." It's critical to "provide value," not just work hard, and define your own American dream.
• Gen Z spotlight: Young people are reconsidering expensive college and traditional paths, turning to trades, entrepreneurship, and redefining “the dream.”

Notable quotes:

“Connection matters more than stuff.” — Joel (06:17)
“Pessimism can be this self-fulfilling prophecy.” — Joel (18:50)
“The crucial way to make sure the American dream works for you is to avoid the major traps...zig while everyone else is zagging.” — Matt (21:20)

5. Loyalty is for Losers: Why Sticking with One Brand Hurts Consumers

(26:55–33:46)

• Ludicrous Headline: “Customer loyalty is a sham” (Business Insider)
• Busted Myths:
  • Longterm loyalty (to insurers, internet, airlines, banks) is often penalized, not rewarded with better prices or perks.
  • Companies exploit inertia—consumers tend not to switch even to their own detriment.
• Real-Life Example: Joel helps a friend save $100/month by switching phone carriers.
• Actionable Tip: Regularly price shop essentials—insurance, cell plans, subscriptions. Use competitor offers for leverage.
• Even Amazon Prime is cracking down on account-sharing, forcing a reconsideration of subscriptions.

Notable quotes:

“We as customers might be getting the short end of the stick because often they don’t offer better perks because we’re loyal. In fact, they take advantage of our loyalty.” — Joel (28:06)
“That’s that inertia bias, which is totally natural...but it could be working against us.” — Matt (30:00)

6. Smarter Holiday Travel Booking (& Google’s “AI” Flight Deals)

(35:30–40:39)

• Peak travel booking tip: Best airfare for major holidays often appears in September—use Google Flights/alerts.
• Flexibility saves: Adjust dates, jump on flight deals, and monitor prices post-booking for potential rebooking at lower rates.
• Google debuts a “Flight Deals” AI beta: Hosts are skeptical—it mostly repackages existing search results, but recommend exploring it if you’re open on destination.
• Travel ethos: First, “find out where it’s cheap to travel”; don’t fixate on one destination.
  (37:09: “Let the deal dictate the trip—it means you’ll spend less and maybe travel more.”)

7. Quick Takes: Tariffs, Market Certainty, and Policy

(40:39–43:01)

• Tariff uncertainty: Recent courts question if the president can unilaterally impose tariffs; so far, economic impact is muted but could grow if tariffs persist.
• Big Picture Concern: Tariffs tend to raise prices and potentially keep interest rates higher if inflation ticks up.
• What’s Next: The Supreme Court may weigh in, introducing more uncertainty for businesses and markets.

Notable Quotes & Timestamps

• “Connection matters more than stuff.” — Joel (06:17)
• “Stay the course, man.” — Matt (10:21)
• “I wish that for individual investors it looked more like Aldi where you walk in and there’s just fewer choices.” — Joel (14:21)
• “Pessimism can be this self-fulfilling prophecy.” — Joel (18:50)
• “The crucial way to make sure the American dream works for you is to avoid the major traps... zig while everyone else is zagging.” — Matt (21:20)
• “We as customers might be getting the short end of the stick because...they take advantage of our loyalty.” — Joel (28:06)
• “That’s that inertia bias, which is totally natural...but it could be working against us.” — Matt (30:00)

Timestamps for Major Segments

• Backpacking, Minimalism & Money Perspective: 03:06–08:21
• Stocks, Market Highs & ETF Overload: 08:21–14:59
• Forgotten 401(k)s: 14:59–16:48
• Peaking Pessimism/American Dream Doubts: 17:16–23:48
• Loyalty is for Losers (Headline/Discussion): 26:55–33:46
• Smarter Holiday Travel & Google Flight Deals: 35:30–40:39
• Tariff Uncertainty & Policy: 40:39–43:01

Episode Takeaways

• Happiness is found in connection and experiences, not just possessions or status.
• Investment FOMO is real, but slow-and-steady index investing remains wise.
• Don’t let 401(k)s go unclaimed—consolidate and reclaim them.
• Define the American dream on your own terms—don’t let inflation or trends dictate your outlook.
• Don’t let ‘loyalty’ cost you money—always price shop!
• Book holiday travel soon, use flexibility and flight alerts for deals.
• Stay tuned to market and policy changes, but focus on what’s in your control.

Engaging, clear, and brimming with timely financial wisdom, this episode is a must-listen for anyone striving to live and invest intentionally—even if that means occasionally questioning tradition or breaking with consumer loyalty.